


Derailed

by Lady Divine Coldflash (fhartz91)



Category: The Flash (TV 2014)
Genre: Alternate Universe, Angst, Coldflash Bingo 2019, First Time, High School, Len is not a virgin, M/M, Sexual Content, Teen Romance, Virgin Barry Allen
Language: English
Status: Completed
Published: 2019-05-10
Updated: 2019-05-11
Packaged: 2020-02-29 13:47:25
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 9,932
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18779506
Author URL: https://archiveofourown.org/users/fhartz91/pseuds/Lady%20Divine%20Coldflash
Summary: Best friends Barry and Len made a pact their freshman year of high school that if they haven't had sex by their senior year, they'd have sex with one another. Barry is still a virgin, but Len has already had sex - lots of sex - so he tells Barry that he feels that makes their arrangement null and void.It's an easy out because he doesn't want to admit just how much in love with Barry he is, and that having him once, then never again, would break his heart.But Barry doesn't take it.





	1. Chapter 1

**Author's Note:**

> Written for the Coldflash Bingo prompt high school au. When I originally wrote this, I was stuck deciding which fandom I would write it for. I ended up posting it for another fandom, but I have always regretted not posting this version for Coldflash. I really like how this turned out. So if you read my other works and this seems familiar, that's why.

“Are you fucking serious?” Len scoffs. He adds a laugh for good measure, hoping his reaction will clear this situation up neat and quick. He’s not intentionally trying to hurt his best friend. It’s more of a fight or flight reflex. He knows Barry is self-conscious. Exploiting that is unforgivable, but what Barry is asking for is unwise in a hundred different ways.

Better to sting Barry once than to burn him permanently.

Barry knows what Len’s doing, but it still works. Not just because Barry has a low opinion of himself physically, but because it’s _Len,_ his best friend (his only other real friend besides Iris, his sort-of-adopted-sister), oddly so seeing as Len used to bully the shit out of him all through middle school. But high school came along and they both discovered they had something in common, something besides track and field and a love of movies based off of comic books. Something that gave them membership to an exclusive club.

They’d both lost their moms at a young age, to a rather brutal and mysterious end.

And even though Len doesn’t have a reputation for being the sympathetic type, that struck a chord with him, especially since the only other member of their club that he knows or cares about is his own sister.

If it were someone else blowing Barry off, someone he admired as much as he admired Len, Barry would still be upset, but he could brush it off.

He can’t brush Len off. He’s tried.

When Barry came up to Len at lunch and blurted out his request, Len spit soda out his nose. Then he grabbed his things, made Barry get his, and they left campus – cut school right before the lunch bell rang and made a beeline for Len’s house. Barry had expected an outright no so he was excited by this turn of events. He thought for sure this meant Len would do it. More than that, that he was eager if they were playing hooky.

But Len has spent the whole walk home trying to talk him out of it.

Barry thought Len might have a few objections, but honestly, he didn’t think it would be _this_ hard.

“I think … I kind of always knew that my first time would be with you anyway, so I might as well, you know, get it out of the way.”

Len can’t look at his best friend after that. “Gee. Thanks.”

“I … I’m sorry. That didn’t come out the right way.” Barry’s eyes fall from the books in his arms to his feet, following the progress of his red Converse sneakers as they travel across the ground with little conscious help from him.

“It’s alright. I think I know what you mean.”

“Len, you are my best friend … aren’t you?”

“Yeah,” Len says quietly. “Yeah, I am.”

“And we agreed freshman year that if we hadn’t had sex with anyone by the time we were seniors, we’d do it with each other.”

“But I’ve already had sex,” Len points out, trying to sound smug, but his voice cracks around the word _sex_ because he’s not exactly proud of it. Once he found someone willing, he kind of became addicted – not just to the act and the pleasure, but the feeling of power that it gave him. He went from being Len Snart - juvenile delinquent and future inevitable career criminal, to Len Snart - sex god. And even though a lot of people might slut shame him, there’s nothing wrong with that, nothing negative he could see, nothing that hinted to his horrid upbringing or any influence from his reprobate father. It’s a reputation Len earned entirely on his own, one that people _envied_.

And he liked the way that felt.

He liked the way boys and girls in school look at him because of it. Even the ones who curl their lips and roll their eyes away – he _lives_ for that reaction.

He liked the way the upperclassmen treat him like one of their own.

He liked the way it keeps kids off his and his sister’s back.

He’s been feared for being Lewis Snart’s kid before, but now, he’s respected.

He’ll take respect over fear any day.

But there came a time when he realized that he gave away something he didn’t know was important to him instead of saving it for someone special.

 _Someone special_ happens to be walking beside him right now, asking him to make good on a dangerous promise. “So doesn’t that make this arrangement null and void?”

“I … I didn’t think of it that way.” Barry’s voice becomes smaller with each word. “You’ve had more opportunities than me. More people want you. I didn’t have that. I still don’t.” Defeat and embarrassment combine in a sigh. “And it looks like you don’t want me either.” He hugs the books in his arms tighter, trying to disappear in the space between his calculus and physics texts.

“Barry. It’s not … it’s not that.”

“It’s all right. To be honest, I don’t know why I thought you’d agree anyway. That pact we made … it was stupid. I should have known better than to try and hold you to it.”

They stop in front of Len’s house. It’s the first one on their route, but Len usually walks Barry all the way home and then doubles back. They stand on the sidewalk, quiet for a few tense moments, before Barry nods, turns on his heel, and starts to walk away.

“It’s not that I don’t want you …” Len’s words stop Barry from taking another step. He reaches for Barry’s shoulder. His hand remains hovering in the air just above. A second later, he returns it to his side. Touching Barry has always been so easy, so natural – a hand on his shoulder, an arm inside his. But having this particular discussion, it seems condescending in a way, like how dads clap you on the shoulder like you’re bosom buddies right before they tell you you’re not old enough to do something. Or, in Len’s experience, that they just plain hate you, that you’re worthless, and they wish you weren’t born. “It’s that … you’re my best friend. When we made that pact, we were kids, not thinking about the consequences of our actions. It seemed like no big thing. But I know what sex between two people can do to a relationship. I don’t want to risk losing your friendship over this. It means too much to me.”

“It won’t ruin it.” Barry can’t imagine how in the world it could. Barry loves Len – like a brother and more. In fact, he can’t see this doing anything but bringing them closer.

Secretly, he’s hoping it will.                   

“I won’t let it. I promise.”

Barry looks back at him, brow pinched in the middle, eyes pleading for him to say yes. But all Len can think is _this is a bad idea_ , but he can’t bring himself to say it. He doesn’t want Barry to think he’s rejecting him for any other reason than he doesn’t want to lose him. But if Barry’s promising, and Barry always keeps his promises …

“Alright,” Len says, the last remnants of common sense flying straight out of his mouth. “Your place or mine? My dad’s … away. He won’t be back for a couple of days, so we have the whole house to ourselves till Lisa gets home.”

“Yours, if you don’t mind,” Barry says biting his lip, virtually bubbling with excitement while Len’s stomach ties itself into fifty knots and migrates to his feet.

Len climbs the six short stairs to his house slowly. He can’t think of any way to stall without tipping Barry off, but he wants to give him time to back out. He begs Barry with significant glances and uncomfortable sighs to change his mind all the way until they reach the front door. Len fiddles with his keys, dropping them once (on actual accident), praying that Barry will get as far as his room and say, “You know what? I changed my mind. I’m not ready for this. Can we watch _Winter Soldier_ instead?” And then that will be the end of that … for today, at least.

But Barry doesn’t.

He dutifully follows Len up to his room, hiding a grin behind his books, his blush unmistakable, skin glowing so hot Len can feel it radiate against his back. Once they get to Len’s room, Barry falters a step on his way to putting his books down, and Len breathes a sigh of relief. _This is it_ , he thinks. The extent of Barry’s courage. He’s had the opportunity to mull things over, seeing as Len took close to fifteen minutes to lead Barry to his room when it normally takes five. But, it turns out, that’s not what’s tripping Barry up.

The real culprit is worse.

“Did you want me to undress myself?” Barry asks shyly. “Or … uh … would you like to … uh …?”

Len clears his throat. He’s pictured undressing Barry a dozen times, sure it would never happen. “I’ll … I’ll do it.”  

Len paces his room. He has to keep moving. He picks up a trophy from his bookcase and moves it to his desk, then moves it back, switching it out for a picture of him and Barry at the lake. Barry is wearing a swimsuit in the picture – a pair of boxy board shorts. He’s also shirtless, which adds insult to injury, especially considering the amount of times Len has used that photograph as masturbation fuel. But not in a creepy way. It’s not all about Barry’s body when Len fantasizes about his best friend. It’s about the things they have in common, and all of the things they don’t. It’s about the jokes they share and the things they do together – the movies they watch, the music they listen to.

It’s about how comfortable they are around one another, even if their relationship didn’t start off that way.

“Did you have an idea how you wanted to do this?” Len asks when he can’t see a way out. He needs to stop thinking about this like a sentence at Iron Heights. He’s not a condemned man.

Not yet.

“What do you mean?”

“Like have you ever watched any movies?”

“Movies?” Barry’s eyebrows lift, the blankest expression overtaking his face. Len imagines Barry racking his brain trying to remember which Marvel movie shows the characters having sex.

“Porn,” Len says, stifling a laugh, not wanting Barry to feel any more humiliated than he’s already made him. Len has a few favorite go-tos on X-Tube. He could whip out his phone and show him, but the fact that he hasn’t offered before now pretty much cements the reasons he won’t.

In some bizarre way, he feels he’s preserving Barry’s innocence.

“A position you want to try?” Len clarifies. “Or a scenario?”

“I … uh … I haven’t given it that much thought. To be honest, I didn’t think I’d get this far.”

“Way to plan ahead, Bare.”

“Well, what would _you_ do? I mean, if you actually wanted to do this with me?”

Len would laugh at that question if he didn’t think it would sound cruel, if Barry didn’t look so on his guard. The truth is Len _has_ a fantasy. _Multiple_ fantasies. Some of them so involved, there’s no way he could execute them now. So he decides to keep things simple. As far as Len knows, Barry has yet to even be kissed – not on the mouth, not the way boyfriends do.

Len feels the whole of his body shiver wanting to give him that.

It seems as good a place as any to start.

He takes a steadying breath. ‘ _Here goes nothing_.’

“Let’s start with this.” Len puts a hand to Barry’s cheek and leans in. Barry jerks away.

“Wait … what are you going to do?”

“I’m going to kiss you, Barry,” Len says, still leaning in.

“Oh.”

“Don’t you want me to kiss you?” he asks, eyes bouncing between Barry’s lips and his eyes. 

“I, uh … uh …” Barry stutters, and Len smiles. He can’t help it. His best friend is adorable when he’s flustered.

No. Len doesn’t want to see him as adorable. Barry is hot. He’s sexy. He’s handsome. He’s incredible, unique, one-of-a-kind.

Unfortunately, he’s all of those things with the innocent, wide eyes of a bichon frise.

In front of Barry’s eyes, his best friend changes – his voice becomes sultry, his eyes go dark, even the palm of his hand caressing his cheek feels hotter. Barry trembles. This is happening. This is actually happening. He can’t _believe_ this is happening.

And it’s happening with Len.

“Yes. Please, kiss me.”

“All right.”

“Wait. Should I … should I count to three?”

“Do you want to?”

“Uh … yes?”

“Then go ahead. Whatever makes you comfortable.”

“Okay.” Barry nods, swallows hard. He’s excited, and though he looks mildly terrified as well, it makes Len excited. This feels like a dream, one he’s had too many times to count. Except it’s real. Barry is here, and considering what Lewis Snart has declared Len’s life will be like after high school, this may be the only time Len gets to have him. “One, two …”

Len doesn’t let Barry get to three. He wants to take him by surprise. He wants to make this unforgettable. If he could have his way, Barry would want him so badly after this one kiss that he’d have no choice but to be his from this day forward. Len knows it would be rough, but they’d find a way. They’d work around life and his dad and the future. In many ways, Barry wanting Len, Barry wanting a future with Len, could be the solution to a great many of Len’s problems.

But Len can’t do that. He can’t put that on Barry. His future happiness, his future stability, isn’t Barry’s responsibility.

Friends. That’s what Barry promised – they would remain friends.

Keeping his best friend is the most Len can hope for.

Len wraps his arms around Barry, sliding his hands up his back till one reaches the base of his head and cradles. Len holds him close, possessively, fitting their lips together as if they had all the time in the world. This is exactly how Barry dreamed of being kissed, how he dreamed of being held. He thought he’d have to search years, be more experienced, before he found someone who could fulfill his fantasy.

Little did he know that that someone was waiting for him behind Len’s bedroom door.

Had he known, would he have come to his best friend sooner?

They part reluctantly with a breath left between them. Barry seems stunned, unable to move as he comes to terms with the fact that he’s just been kissed – a  _real_  kiss, the first ever of his life. But something about that kiss gets under Len’s skin. It motivates him. He _wants_ this. He’s always wanted this. He longs to feel Barry’s body against his, feel his heart beating against his chest as if it were his own. He doesn’t want power over Barry, not like he has with other lovers. Quite the opposite. He wants to give himself to Barry. He wants a first time with Barry. He wants to make this good for him, for the both of them. He knows he can.

He doesn’t want to rush, but he can’t wait to get started.

Len kicks off his shoes and pulls off his socks. He tosses off his jeans, followed by his shirt, his undershirt, and his briefs, and suddenly, as Barry watches, it becomes too real. There are things happening, things he’s seeing, that he never anticipated, that he wasn’t prepared for. The first, and probably the most jarring, is Len naked. Completely naked. And not naked like shower-in-the-locker-room naked, but aroused naked, which is a thousand percent different – Len’s heavy breathing, the dark look in his eyes, the rosy flush to his skin, the hair between his legs, and his cock, hard and bobbing, leaking at the tip. Leaking because of the prospect of having sex or because of  _him_ , Barry is reluctant to ask. But these are things that Barry never included in his fantasies because it never dawned on him to add them.

And he especially never thought he’d see them on Len.

“Are you okay?” Len asks, more worried than flattered by Barry’s drop-jawed expression and held breath.

“Wha---what?” Barry gives himself a mental shake. “Yeah. I’m great. P-perfect. Fine. Why?”

“You were so gung-ho when we got here, but now you seem stuck on stupid.”

Barry hates that term ‘stuck on stupid’, but it’s the disappointment in Len’s voice that brings him out of his stupor. Barry doesn’t know what changed Len’s mind, why he’s so eager, but he’s definitely not about to look a gift horse in the mouth.

“I … I just … I guess I didn’t realize …”

“Didn’t realize what?”

“I didn’t realize how …” Barry has to stop himself from looking Len over from head to toe for the eighth time. He doesn’t want to be rude, but _Jesus Christ_! “… how handsome you are.”

“You’re just saying that,” Len replies, taking himself by surprise. He has no doubts about his looks. He doesn’t spend hours preening in the mirror or anything, but he still prides himself on them. He’s had other boys and girls call him handsome and more. But hearing it from Barry, in the heat of this moment, makes it feel truer.

“I’m … I’m not.” Barry shudders as Len reaches out for him, toying with the hem of his shirt, creeping it up his stomach. “You … you are. And I …”

“You’re handsome, too, you know.” Len lines Barry’s lips with kisses as he slips the shirt over his head.

“Not like you,” Barry admits, lifting his chin as Len moves down his neck. “I’m not as … as athletic … or as …”

“Shhh. Don’t …” Len hushes him as he travels down his body. He’s used to Barry’s self-deprecating commentary, but he can’t listen to it now. Len has seen boys with gorgeous bodies before. But Barry’s is gorgeous in ways that Barry refuses to see. Len wants to show him that even if other kids at their school are ignorant enough to overlook the wondrous things about him, one person hasn’t.

One person hasn’t for years.

Barry happens to have Len’s favorite body type. He doesn’t spend hours in the gym like some guys, trying to turn into something he’s not. His lean muscles and flat stomach come from  _living_  – eating right, walking everywhere, and running track. But he’s soft in places, too, the way a boy his age should be. He’s not trying to grow up too quickly – today’s request notwithstanding.

But who is Len to judge? He was a sophomore when he had his v-card punched.

Barry held out till senior year.

Barry is tempted to peek down at Len as he makes his way south, peeling down his jeans and underwear as he goes, but he’s paralyzed. He’s not scared. Anxious, but not scared, not anymore. It’s easier for him to lose himself this way, separate himself from his apprehensions and simply focus on what his best friend is doing to him. He worries about how he smells or tastes. That’s another thing he’d never considered, but it’s a very real concern to him at the moment. He does have one thing going for him.

They didn’t have P.E. today.

But Len doesn’t go that route. He seems married to the task of getting Barry undressed. Once he pulls down Barry’s briefs, he takes a few moments to appreciate what Barry has – what no one but his doctor has seen. He kisses down Barry’s shaft, licks a few times around the head, but leaves it at that, and Barry is relieved. Unpleasant tastes and smells aside, considering how his cock responds to that touch, had Len taken him in his mouth, he’d probably shoot straight down Len’s throat in seconds.

Barry doesn’t want this to be over, not when it nearly took an act of Congress to get him here.

Len kisses a trail back up Barry’s body and finds his lips again. Len’s amazing mouth occupies Barry’s mind completely, tugging gently at his lips and constantly whispering his name – “Barry … oh, Barry …” Strong arms move him to the bed. He registers the sensation of floating until he lands on the mattress, Len’s comforter and pillows underneath him.  

“How are we doing this?” Len asks, his husky voice in Barry’s ear the thing dreams are made of.

“Wha---what do you mean?”

“I mean - me in you, or you in me?”

“Uh … you in me? I don’t think I’m ready for the other way just yet.”

“Fair enough.”

Len normally doesn’t give his male lovers a choice. He’s not too fond of being entered, though he has been a couple of times. It’s nothing more than personal preference. But for Barry, he’d do it.

He’d do anything for Barry.

Len continues kissing Barry, pressing their bodies together, covering Barry’s body with his own so he can be full of him. He raises Barry’s arms above his head and pins them at the wrists, only letting go to reach somewhere out of sight and grab a condom and a bottle of lube. Barry is curious where he had those stashed since they seemed nearby and at the ready, but he doesn’t want to be the one to break their kiss and find out. Len eventually does, turning his face to the side and tearing open the condom packet with one hand and his teeth. Barry inhales quickly in anticipation, then scrunches his nose.

“What?” Len asks, kneeling to roll the condom down his length. Barry watches, a little less mystified but eyes still glued to the act.

“I just … I didn’t think condoms would smell like that.” Barry takes another sniff, the odor more pungent now that it’s unrolled, and makes a noise. “It’s sort of … gross.”

Len has a remark but he holds back. This is Barry’s first time, his first experience with anything sexual really. Len has used so many condoms, a lot about them has escaped his notice. Barry is a scientist at heart. Observation is kind of his thing, no matter what the situation. Len can’t shoot down everything Barry says.

He gives himself a second to think about it. He takes a breath in. His nose scrunches, too.

Barry is right. They do smell gross.

“Yeah, alright,” he concurs. “But they’re a necessary evil, so try to overlook it.”

Len goes back to kissing Barry, as Barry had hoped, but instead of holding his wrists above his head (which Barry kind of liked), he’s toying with the bottle of lube. Amidst Len’s intoxicating kisses, Barry’s heart starts to pound. It’s a turn on for Len, feeling Barry’s heart drum over his own, but for Barry, it’s more of a cry.

As much as Barry wants to have sex, this is the part he’s looking forward to the least.

There’s no amount of bracing in the world that’s going to prepare Barry for this.

Len anticipates resistance. It happens during most first times, even with boys who finger themselves in private. But Barry’s lower half literally turns to stone. Once Len gets past Barry’s pinched cheeks, he finds his entrance, the muscle squeezed so tight it feels like circling solid rock.

Len tries everything he can think of to get Barry to relax – kisses to his neck and shoulders, sucking on his nipples, even a few more licks around the head of his cock. But the more he tries to touch his rear, the more he massages and strokes, the tenser Barry becomes. Len sighs. All of this anxiety, all of this doubt, all of this mental negotiation and gambling, and he’s stuck right at the starting gate.

“Barry, you’re gonna have to relax.”

“I---I am relaxed,” Barry says, his voice jumping an octave.

“Do you think you could get  _more_  relaxed?”

“Like … how much more?”

“Well, at this rate, maybe you should be asleep for your first time.”

“Ha-ha. Very funny. Can’t you just … shove it in?”

“Yeah, if I wanted to bend my dick in half. Or tear something. I don’t want to hurt you, Barry!”

“I know, I know.” Barry grinds his teeth till his head starts to throb, on the brink of laughing and crying at the same time. He knew that his first time might be problematic and that it could hurt, but he didn’t know it would be this difficult. He didn’t know that his body would reject Len’s attempts at entering it. It’s never like this in the movies. He’s only seen a handful of NC17 rated rom-coms (forced on him by Iris), but they make it seem like, if you can get your clothes off, everything else just sort of falls into place. “It’s just … this is so weird.”

“Weird … because of me?”

“No!” Barry answers quickly. “No, not because of you! Not at all! It just … it doesn’t feel natural. Or particularly sanitary.”

“Look …” Len takes a breath, biding his time to think, which is impossible when his body, for one, is ready to go. He should call it quits, convince Barry that sex – at least, penetrative sex – isn’t all it’s cracked up to be. He could just blow Barry. Regardless of what the girls at Central City High like to tell one another, oral sex is still sex. It’s right there in the name. As far as Len is concerned, if he blew Barry, that would still count as him losing his virginity.

But he knows that’s not what Barry wants.

In the middle of Len struggling with this conundrum, Barry begins massaging his shoulders, drawing lines between the freckles on his skin with delicate strokes of his fingertips. It feels too good. Barry’s touch is so unpracticed but so familiar. Len doesn’t want it to end. But he has to turn Barry over, get him on his hands and knees if he has any chance of entering him. He’d given it a go with Barry lying on his back because Len thought that would be more intimate. He could kiss him on the lips, look into his eyes.

If Barry would agree to make out with him for the next hour or so while Len gave him a hand job, they could still do that. Maybe that would be a decent compromise?

Len watches Barry’s frustrated face morph into a hopeful expression. Barry deserves more than a compromise. He deserves this, if this is what he wants.

“Concentrate on relaxing,” he says, taking Barry by the shoulders and turning him over. Barry complies, flipping first on to his stomach, then rising to his hands and knees when Len pulls up on his hips.

“O---okay,” Barry mutters. “I’ll … I’ll just relax.”

“Good. Deep breaths.”

“Deep … breaths,” Barry repeats as Len begins to touch him, begins to kiss him, begins to run a slick finger around the entrance of his hole and try over and over to seduce him open. He sucks lightly at Barry’s neck. He finds a spot below Barry’s right ear that makes him melt and finally manages to slide his index finger inside. He crooks it, then slowly works it in and out, adding another without asking when he knows Barry is ready. Slowly, patiently, he unlocks places in Barry’s body that Barry didn’t know existed – places of pleasure so extreme they’re almost too embarrassing to enjoy.

There’s a pause, and an emptiness when Len removes his fingers, but that’s replaced by an overwhelming fullness when Len starts to enter him, inch by inch in and out, punctuated by the most sinful sounding moans in between.

“Oh God, Barry … oh God … you feel … so incredible …”

Barry tries to respond. He opens his mouth, compliment on his tongue. But as Len moves, snapping his hips in a smooth and steady rhythm, those words dissolve. What Len is doing to him feels sublime.  _Too_  sublime. And a lump, like coal, forms in his chest, burning in his heart.

Barry knows that his best friend isn’t a virgin. He didn’t ask for details, but he knew that Len had been having sex with other students from Central City High regularly up until a few months ago. It bothered Barry, but he didn’t dwell on it. Or he tried not to. It wasn’t a part of their relationship together. Len didn’t kiss and tell, so it was easy for Barry to pretend like Len’s sex life was as non-existent as his own.

They aren’t two virgins fumbling their way through this act together.

It isn’t until Len starts fucking him that Barry realizes exactly how experienced his best friend is.

“That’s it, baby,” Len says. “Just relax and let go. I’ll make you feel good. I promise.”

And Len does. He does things for Barry he’s never done for anyone. He kisses him gently, explores his body with his hands and his tongue, hugs him, holds him, never more than a few inches apart from him.

He doesn’t have sex with Barry. He makes love to Barry. And that’s a first for Len.

But Barry doesn’t know that. He doesn’t know that this time, for Len, is significant.

“God, Barry,” Len moans. “I’m going to cum, I swear …”

“M-me, too,” Barry mumbles, not convinced he is. He feels like it, heat building up inside him the way it has on the few occasions he’s masturbated, but he’s not quite there yet. He needs a little something more.

“Are you sure?” Len asks, winding an arm around Barry’s waist and reaching for his cock. The second his fingers wrap around and hold, Barry gasps. His eyes pop, his jaw drops, and everything comes into focus.

“Oh, God,” he squeaks, his mind dropping out of existence. He feels like he’s levitating, the only thing keeping him from lifting away into the atmosphere - Len’s arm around his waist.

Len starts to stroke. He must feel the waves rolling through Barry’s body because he speeds up. He braces himself with one arm against the wall and yet still manages to kiss Barry tenderly on the back of the neck. The fact that he can do it all at the same time leaves Barry in awe. But then he remembers – Len can do it because he’s had practice. Because he’s done this before.

Because Barry isn’t his first, and he probably won’t be his last.

And that thought nearly ruins Barry’s orgasm.

As it is, it’s stunted compared to what he thought it would be, but it’s still better than anything he’s ever experienced alone.

Because he’s with someone who knows what they’re doing.

Because he’s with  _Len_.

Barry has always considered himself mature for his age – more mature than his best friend by far. But now, on his hands and knees beneath Len’s body, he feels more like a teenager than he has in a long time. As Barry cums in Len’s arms, his head dropping forward with Len’s forehead pressed against his neck, Barry can’t help but wonder – was Len’s first time like this? Why did he do it? Barry feels vulnerable right now, painfully so. Len isn’t the vulnerable type. Why would he make himself this vulnerable to someone? Why would you do this with someone unless you loved them, heart and soul?

Oh God! Did Len love the person he lost his virginity to? Barry doesn’t think so, but he can’t be sure. How does Barry not know for sure?

Shame washes through him as he realizes he doesn’t know for one reason and one reason alone.

He’s selfish. Len tried to talk to him about it after it happened but Barry kept changing the subject. The few times Len got a sentence through, Barry tuned him out. He didn’t want to know. He didn’t want to imagine his best friend in that position. Barry would sit and listen to Len talk for hours about everything else in his life from missing his mom to his father’s abuse to how much he worried about his sister … but not this. It was the only real boundary they had in their relationship.

And it was created because Barry is the worst friend ever.

So much for being the mature one.

Len wraps his arms around Barry’s chest and rests his head against his shoulder.

“Oh, God … oh, Barry …” he groans, sated.

Relaxed.

Satisfied.

And even though Barry came, he doesn’t feel any of those things.

Barry stops breathing. He starts hyperventilating. He covers his face with his hands.

What has he done?

He thought he could do this, thought he could remove himself from his deeper feelings about Len, or indulge in them safely, and get this over with, but he was wrong. He was naïve and wrong and now …

“Barry?” Len’s purrs against Barry’s neck stop. “Are you … are you okay?”

“No,” Barry mumbles through his fingers, nails digging into his hairline. How could he be so stupid?

“What’s wrong?”

Barry shakes his head. What is he supposed to say? How does he tell his best friend that this wasn’t about some dumb pact? That it wasn’t really even so much about losing his virginity? That he wanted to have sex with Len because he knew he couldn’t have him?

How does he look at Len after today? How does he bear the pain when Len finds a new conquest?

“I’m … no. I’m sorry, Len.”

“What is it? Are you hurt?” He looks Barry over, searching for any marks or bleeding, some sign of an injury.

“No, I’m not hurt,” Barry lies. “I … I was wrong. This … it wasn’t what I wanted.”

“Barry …” Len puts a hand on Barry’s shoulder, but Barry recoils.

“P-please. Please, I … I need a minute to myself. I need to ...” Without finishing, Barry slides off the bed, avoiding Len’s touch as he collects his clothes and puts them on – underwear, t-shirt, jeans - ticking them off in his head so he can keep his mind away from what happened.

“Barry?” Len pulls on a pair of navy sweatpants and a white t-shirt in less time than it takes Barry to reach the bedroom door. “Barry, don’t … please, don’t leave.”

“I’m sorry.” Barry grabs his books, worrying the soft corner of his math book with the tip of his index finger, his eyes locked on the door. He’s not itching to leave. Len’s room is as comforting to him as his own when Len’s dad isn’t around.

But he can’t stay.

“I can’t … I can’t be here right now.”

“So, that’s it?” Len steps back, crossing his arms in front of his chest, jaw locked, eyes suddenly rock hard. “You’re just going to leave? You got what you wanted, and now you’re out the door? You said this wouldn’t ruin our friendship, but that was just a lie, wasn’t it? A fucking lie! You’re just like everyone else, aren’t you, Barry? I should have fucking known! I should have known! I’m so stupid, I …” Len goes dumb, mouth hanging open, shaking his head. He tries to stay cold. He wants to be mean, but he can’t. He thought Barry was the only person in his life he couldn’t scare away, the only person his dad couldn’t take away. The only person who’d stick around no matter what. Boy, was he wrong. And maybe it would be better off for the both of them if Len told him to leave and never come back, but he can’t bring himself to do that. Because Barry isn’t just another lover. He’s the boy that Len _loves_. “Y-you … you can’t go! Y-you’re the best friend I have, Barry! Please, don’t leave! Not like this! I … I can’t lose you, Barry! I can’t …!”

Len chokes on the end of his sentence. Barry turns around and looks at his friend – desperate, frantic, heartbroken. Barry’s head tugs him towards the door in an effort to protect himself, but his heart is leading him back. Barry has always been the kind of person to follow his head before his heart, no matter how painful that’s been for him in the past, but not this time.

Not when something more important than both is on the line.

Barry wasn’t alone in this. He didn’t spend the past hour fucking himself. There was someone else, a reluctant participant whose feelings Barry hadn’t considered as much as he should have.

A boy who Barry loves, who made his first time magical.

A boy who Barry will have used inexcusably if he walks out the door.

Len may have started out the bully when the two of them met back in middle school, but it’s Barry who turned out to be the jerk.

He puts his books down.

“You’re right.” Barry sniffs. “You’re absolutely right, and I’m sorry.” He walks over to his friend and wraps his arms around his waist. “Please … hold me?”

Len’s arms move in slow motion, winding around Barry’s body, hurt feelings making him insecure. But as soon as he feels Barry’s warmth, he holds him tight, rocking him in his arms. It feels nice to hold Barry like this.

It feels damn near close to perfect.

Len wants this for as long as he can have it, but he doesn’t know how to make that happen, not when he narrowly stopped Barry from bolting out the door.

“What do we do now?” Barry asks.

“I don’t know, but please tell me you’ll stay so we can work this out?”

“I will.” Those words work their way into Len’s soul and he holds Barry tighter. “I promise.”

 

 


	2. Afterglow

**Summary for the Chapter:**

> After Barry's first time with his best friend, Len, the two boys realize that there is too much unsaid between them to leave things the way they are. But will talking about it bring them together ... or push them apart?

**Notes for the Chapter:**

> This is a re-write, but I think it works well here. :)

_Len’s fingers trail slowly up Barry’s sides, slipping underneath his t-shirt to slide the fabric up his body. Barry does the same to Len’s shirt, but with fingers that tremble as they go, unintentionally spreading goosebumps along Len’s skin. When Barry’s fingers reach the spot just below Len’s armpits where his ribs curl towards his pecs, his elbows clamp down tight to his sides._

_“Op! I forgot you’re ticklish!” Barry says, juggling a giggle and a gasp as Len retaliates by lightly licking his neck. Barry squirms to get away, but Len puts a hand to his cheek and holds him in place._

_“Yeah” - Len grins, sucking on the one spot he knows will make Barry squeal like a piglet - “but I didn’t …”_

***

“What was your first time like?”

Len inhales deeply, then sighs into the air above him. This isn’t the conversation he was hoping they’d be having when they finished hugging and returned to Len’s bed. He’s not in the mood to talk about this, though he can see how the current atmosphere might have lead them in this direction. He’d wanted to talk about it when it happened, and definitely with Barry, but Barry made it clear that he wasn’t comfortable with the subject, and Len let it drop. He figured he’d shoot the shit with one of his other friends another time. But when it came up one afternoon after wrestling practice, strangely enough, it seemed too personal. As much as Len couldn’t care less about locker room talk when other guys did it, he didn’t want to participate. It seemed tacky and immature. As it turned out, people didn’t need to hear about his exploits from him. The gossip mill more than did the work for him, and he was fine with that, especially when that talk exaggerated details in his favor.

This isn’t going to be locker room talk. It’s a sore spot for the both of them.

At least they’re talking here and not over the phone.

At least Barry stayed.

“I thought you didn’t want to hear about it,” Len says in a wry rendition of his best friend’s voice.

“Yeah, well, I’ve come to the conclusion that that might have been a jerk move on my part.” Barry rolls his head to the side to look at Len, eyes full of regret. “You’re my best friend. That was a big step in your life, I assume. You should be able to talk to me about it.”

Len tightens his grip on Barry’s hand, partially for security, and partially so Barry doesn’t let go when he hears the answer. They’re about to enter touchy territory, even if it is ancient history as far as Len is concerned.

“It was okay, I guess.” He shrugs, then turns his head to meet Barry’s gaze. The two stare at one another in silent challenge - Len praying Barry will change the subject, Barry waiting patiently for more. Len blinks first. He sighs again. Here he is, stuck in another situation he sees no way out of. But if there was ever a time for him to bear his soul, now is that time. If he had told Barry originally how his reluctance to let Len confide in him had hurt him, they might not be in this position, good or bad. “Honestly, it was pretty awful.”

“How?”

“I met her outside _Saints and Sinners_. She was a professional, and I had no clue what I was doing. I screwed up trying to open the lube and made a huge mess all over her skirt. We were in an alley, upright against a wall. I scratched my calf on a piece of metal and had to get a tetanus shot.”

“Ouch.”

“Yeah. It cut pretty deep. I have a nasty scar.”

Barry knows that scar. He’s seen it plenty during P.E. He thought for sure it was something his father gave him. He’s relieved to discover it isn’t, regardless of its source.

“So, not someone from our school? And not a guy?”

“Nah.” Len looks sheepishly down at the comforter beneath them, eyes tracing a line of stitching close to his face. “She said she was twenty-one, but I don’t think she was. She seemed younger … closer to our age. I kept thinking that, if my dad had his way, then Lisa might be standing there, hitting guys up, people he works with even …” Len swallows hard, squeezes Barry’s hand tighter. “Anyway, she doesn’t go to school with us. I’ve never seen her again.”

Barry has to admit he’s relieved. He had thought all of Len’s sex partners were boys and girls from their school. Seeing their faces every day, how they watched Len in the hallway with wide, puppy-dog eyes, forever hoping he’d glance their way, stung. Barry didn’t know how he would handle finding out which one of those constantly pleading students was Len’s first.

Knowing that none of them were is a huge weight off Barry’s shoulders, but it’s in no way the better of two evils.

Casual sex is one thing, and yes, virginity is a stupid societal construct that shouldn’t amount for anything, so technically your first sexual experience shouldn’t hold any more weight than your last.

Call him a sentimental fool but, to Barry, in some ways it does.

In retrospect, the reason why Len never did look their way was usually because he and Barry were together, and Len was looking at him.

***

_Len kisses Barry tenderly, urgently, possessively, passionately, each one translating want and longing and desire in ways words could never properly express. And between each kiss, he gazes into Barry’s eyes, brow pulled in the center as if he can’t believe that Barry is there. But he is there, and they’re together, making love on Len’s bed the way Len had dreamed of so many times. All he has to do is reach out and touch him - Barry’s soft skin beneath Len’s fingertips proof of his existence in this fantasy come to life. Now that he has Barry, there are no others. His past is just that – the past. And it’s gone, erased completely every time Barry kisses him back, looks him in the eyes, and smiles – blissful, bashful._

***

“Were you safe?” Barry asks, digging deeper for his own peace of mind. Maybe Barry should be a bit more sensitive considering they’re talking about the person Len lost his virginity to, but someone he met outside a _bar_? Barry can’t imagine Len, of all people, being so careless.

Len may be daring, but he’s not reckless.

Then again, there are days he comes to school with his eye black and blue, looking so done with life that Barry spends the whole day by his side, just to make sure he doesn’t do something _reckless_.

“Of course, we were,” Len admits with some embarrassment. He knew that Barry would scold him over this if he ever found out, but he was confident Barry never would. Besides, he’d shouldered that responsibility, berating himself plenty for losing his virginity to some rando on the street. But it had been a game to Len. His father was inside, settling up a score, and Len was trying his hand at acting tough out in the real world, where most people see his dad as the big bad and Len as his obedient lap dog. He didn’t have anything to sell, he wasn’t going to negotiate a heist. When it came down to it, propositioning a prostitute for sex was the only thing he could come up with at the time. He needed a way to raise his street cred. In a sick way, he thought it was something his dad might be proud of. “I swear. I made sure I took condoms with me when I went,” Len defends himself quickly, but his voice peters off when he realizes how bad that sounds, how it cements the idea that he’d gone to  _Saints and Sinners_  on the lookout for a fuck when that wasn’t actually the case “… you know … just in case ...”

Barry stops himself before he can huff or make some other judgmental noise. Barry started this. He’s clearing the air. It’s important to him. He doesn’t want there to be secrets between them. But honestly, Len isn’t required to answer him if he doesn’t want to. Barry should be grateful that Len is willing to give him a second chance at being the friend he should have been years ago.

“So, it sounds like you were on a mission,” Barry teases to break the tension.

“Yeah.” Len chuckles tensely. “I guess … I guess it does.”

“Mission accomplished?”

“No,” Len says, and it’s true. It was true then, and it’s doubly true now. “If I could take it back and replace it with what we just did, I would in a heartbeat.”

***

_“Whoa … no-no-no … oh … whoops!”_

_Len over-enthusiastically rips open the condom wrapper, fumbles the lubricated disk, and sends it flying across the room. Both boys watch it, snickering as it disappears in a corner behind Len’s desk. Barry falls back on the pillows and snorts while Len, laughing just as hard, struggles to catch his breath._

_“Well, that’s never happened before.”_

_“There’s a first time for everything.” Barry reaches for Len’s stash of condoms that he keeps under his pillows. Barry had raised an eyebrow at that when he saw Len fish one out, and the sheepish expression returned to Len’s face._

_“Uh … I keep them under there just in case,” Len had said, darting his eyes, unable to decide on a spot for them to settle._

_“Who were you expecting?”_

_“No one! I swear! It’s been a few months and I … kind of forgot they were there.”_

_“Ugh!” Barry groaned._

_“What?”_

_“How long has it been since you changed these sheets!?”_

_Len didn’t answer, but the conversation at large had been swept under the proverbial carpet when Len began rutting against Barry, convincing him with long sweeps of his tongue over the sensitive skin at the juncture of his neck to forget about it._

_And Barry, melting into a potentially filthy comforter, did._

_Len goes to take the condom from him, but Barry palms it._

_“Can I?” Barry asks, gesturing towards Len cock. “Do you mind if I try …?”_

_“No.” Len gulps so hard he’s sure he’s shoved his heart down a foot. “Not at all. G-give it a try.” He kneels up, straddling Barry’s hips to give him space to work. He watches Barry pinch the tip the way their teacher showed them in health class, place it gently over the head of Len’s cock, and roll it down with excruciating slowness. He rolls it to the base of Len’s cock, then runs a hand over it to remove any air bubbles._

_“There.” Barry looks up at Len for approval. “Is that … is that okay?”_

_“Okay?” Len winds his arms around Barry’s torso, squeezing him so hard he cracks his spine. “It’s more than okay! I think that’s the hottest thing I’ve ever fucking seen!”_

***

“Wh--why did you do it?”

This is the question.  _The_  question. Len can tell by the sound of Barry’s voice when he asks it. This is the one he’s been waiting to ask, the one he’s probably been dreading. The one that had festered in the back of his mind every time Barry saw Len a morning after. It was on those mornings that Len should have realized how much he was hurting Barry. But sex doesn’t equal love … or maturity, and when it came to Barry and his feelings, Len had a tendency to be a little bit naïve.

He’d thought that, when it came to pining over Barry, the only person he was hurting was himself.

“A lot of reasons. I thought it would make me feel more adult. And I was curious. I wanted to see what all the fuss was about. And, kind of like you, I wanted to get it over with.”

Barry’s hand goes rigid in Len’s grasp and he can’t understand why until he remembers what Barry said to him in his car on the way over:

_“I think … I kind of always knew that my first time would be with you anyway …”_

What if that wasn’t resignation? What if Barry had been waiting for him? Subconsciously saving himself for him? Barry said that other kids don’t want him, but what if that isn’t entirely the truth? What if Barry can’t see the ones who do because he wanted Len first?

Len had wanted Barry, too. He just didn’t wait for him.

***

_“Now, are you sure about this?”_

_“Are we going to go through this again? Because it was exhausting the first time.”_

_“Yes,” Len says. “I don’t want to hurt you. I mean, you just did it for the first time about fifteen minutes ago. You have to be sore.”_

_“Maybe a little …” Barry makes a face when he shifts to the side and a throb in his ass confirms that yes, he is sore. “But not too much. Just … go slow.”_

_“You know, we don’t have to have sex the way we did before.” Len bends low to Barry’s ear, whispering in that dark, seductive voice that was so startling to Barry when he first heard it, but which sends all sorts of delicious chills up his spine. “I can suck you off. It’ll be just as good. I promise.”_

_Barry bites his lower lip, tempted by the offer, but confused by the ball of hot and hurt that statement puts in his stomach. He shakes his head. It’s an answer, but it’s also an attempt to brush that ball aside._

_“Maybe some other time? I really, really want this. Unless you … you don’t …”_

_Len rushes forward and collects the end of that sentence in a kiss. “Barry, there won’t ever be a day when I don’t want to make love to you.”_

***

“Were any other times awful?” Barry asks while Len wrestles with his conscience.

“A lot of the times were. It’s just an act when you don’t feel anything for the person you’re with.” He raises Barry’s hand to his mouth and kisses it. “It’s better with feelings.”

Barry licks dry lips, chewing around a smile. “Then, why did you keep doing it?”

“Because, physically, it felt good. It’s great for stress relief. And besides, once you have sex, you kind of feel pressure to keep having it, whether you want to or not.”

“Was there ever anyone you were with that you liked? I mean, that you wanted to be boyfriends with?”

Regardless of what Len believes, _this_ is actually the question. The one that fills Barry with fear. Len may have had sex with a lot of kids at Central City High and beyond, but there was one person in particular – Valerie. She was an upperclassman, cheerleader, gymnast, Prom Queen two years in a row, the girl that’s on everyone’s radar. To make matters worse, she wasn’t stuck-up or bitchy. Then Barry could hate her. She was a genuinely sweet girl, had her sites on becoming an investigative journalist, maybe even a D.A. Wanted to take a year off after high school to join the Peace Corps.

If Len could have hit the lottery hooking up with anyone at their school, it was her.

As far as Barry knows, Valerie was the ‘fuck buddy’ Len was with off and on the longest. He loathed the day he’d find out the two of them had decided to make their undercover relationship official. But Valerie graduated last year. They hadn’t heard from her since, and as far as Barry could tell, Len didn’t seem to mourn the loss.

Of course, Len is good at keeping his true feelings hidden, even from Barry.

Barry might be able to overlook the sex if Len didn’t like any of his partners enough to date them. God, that sounds awful, but some of the truest things in life do.

“No,” Len says in a tone that Barry has no reason to doubt. “No one.”

“Really?” Barry asks, because even if he doesn’t doubt him, he needs to make sure.

Len smiles suddenly, looking at Barry with a twinkle in his eyes. “Actually … uh … does today count?”

***

_It’s easier entering Barry now that he’s open, that he’s comfortable with being touched. He knows Len’s fingers, knows what they’re going to do. It’s a touch he invites. It doesn’t feel awkward or unnatural now that he knows what to expect. Len uses twice as much lube as before. He knows that Barry’s sore, knows how sore he has to be, even if he’s good at not showing it. If there’s one thing Barry has always been expert at hiding, it’s pain. But now Len can give Barry the experience he’d wanted him to have._

_He can look him in the eyes._

_He can kiss him on the lips._

_He can be face to face with him when he tells him he loves him._

***

“What makes me different?” Barry asks, figuring he’ll give Len a break in the form of an easy question to answer. They’re best friends, have been for close to a decade. They’re comfortable with one another. They’re compatible.

Isn’t there a saying about dating your best friend?

“The difference is …” Len runs a thumb over Barry’s knuckles. He has to keep touching him, has to keep reminding himself that what’s happening is real, that with every question he answers, he gets closer and closer to something he’s wanted for a long time “… I love you, Barry.”

“I love you, too.”

“No. I mean … I love you. I love you more than anyone I’ve ever met. And the idea that you’re going to find someone down the line and … and fall in love with them … make love to them …” Len turns his face to the ceiling, fighting a well of angry tears “… maybe it makes me a hypocrite but, it kills me. Every time I picture it, I want to burn my eyes out. You know?”

Barry could agree. He could admit he feels the same. He could lay on Len’s shoulders the depth of his despair since he began having sex. But he doesn’t want to guilt his best friend. He’s not about to shame him for his choices.

Len has nothing to be ashamed of.

Besides, had Barry been honest with Len earlier, maybe things would be different now.

“Actually, I’m already in love with someone,” Barry confesses. Len’s face falls, but only for a second before Barry scoots a little closer, and Len’s cheeks begin to burn. Barry isn’t used to seeing his best friend blush. He’s beginning to enjoy that shade on him. “I have been for a while now. I just … I never had the courage to tell him.”

“Do you think you might tell him soon?” Len asks, moving with Barry, curling in towards him and wrapping an arm around his waist.

“I think so,” Barry says. “Very, very soon.”

***

_“I love you, Len. I … I love you. God!” There’s a freedom in Barry’s voice, a brand new lack of shame when he says, “I’m cumming … oh God …”_

_“I love you, too,” Len whimpers, speeding his hips to stay in sync with Barry so they can cum together. To think, this entire time, they’d been on basically the same page and never knew it. Well, that stops today. As far as Len is concerned, there isn’t a single thought he has about their relationship that he will keep to himself again._

_He pauses to move an inch closer, his pounding having slid him too far down the mattress, to discover that Barry refuses to simply lay docile on the bed. He starts pushing back, meeting Len’s hips thrust for thrust, and that puts Len over the edge._

***

“Do you  _want_  to be my boyfriend?” Barry asks. “I mean, we’re going to college next year. Everything could change for us.”

“ _You’re_ going to college next year,” Len says bitterly. “Me … I’m never gettin’ out of Central City.”

“You will. I have faith in you.”

“You’re gonna need to have faith for the both of us then.”

“I will. I promise.”

“Yeah? And you always keep your promises.”

“I try, at least.”

“I want to be your boyfriend,” Len admits. “I only want to be with you, but … we can’t be public about it. My dad, if he found out … he seemed fine with me foolin’ around, but if he found out I had someone on the steady, and that it was you … with Joe being a cop and all …”

“I understand.”

“But it shouldn’t have to be that way. You deserve more.”

“I’ll take what I can get. We only have the next few months together. I’m willing to give it a try if you are.”

“I am. And I want to, more than you’ll ever know.”

“Then can you do me a favor?” Barry asks, his stomach quivering like the first time he ever spoke in front of the Greater Minneapolis Science Symposium … or the times he told a disbelieving room full of police officers what really happened to his mother the night she died. But he’s ready to jump into this relationship with both feet, even if his stomach decides to leap out of his mouth and leave him entirely.

“What’s that?” Len asks, curious about Barry’s terms and conditions seeing as he’s outlined his own.

Barry puts a hand to Len’s cheek, pulling him closer, gaze flicking down to his lips, then back to his eyes. “Make love to me again?”

 


End file.
